i) Compounds per se
Very few 2-hydroxyalkenoic acids have been reported in the literature. These are:
2-hydroxy-4-hexenoic acid, whose synthesis is described in a paper by Mikami et al entitled "Novel silyl triflate-mediated [2,3] Wittig sigmatropic rearrangement. The possible interpretation of an oxygen ylide", published in Tetrahedron Lett. 1986, 27(37), 4511-14, and abstracted in Chem. Abs. (1987), 107, 77286h. PA0 2-Hydroxy-4-heptenoic acid, whose synthesis is described in a paper by Achmatowicz et al entitled "Monoenic syntheses. I. On monoenophilic reactivity of ethyl mesoxalate", published in Roczniki Chem. 36 1791-1813 (1962), and abstracted in Chem. Abs. (1963), 59 8610d. PA0 2-Hydroxy-4-octenoic acid, whose synthesis is described in a paper by Brenner et al, entitled "Some aspects of the chemistry of 1,1,1-trihaloalk-4-en-ols, the ene adducts obtained from reaction of chloral and bromal with alkenes", published in J. Chem. Soc., Perkin Trans. 1 1984 (3), 331-42, and abstracted in Chem. Abs. (1984), 101. 38095b. PA0 2-Hydroxy-4-dodecenoic acid, whose synthesis is described in a paper by Takeshi et al entitled "Application of [2,3]sigmatropic rearrangements in organic synthesis. 111. The [2,3] Wittig rearrangement of 2-alkenyloxyacetic acids and its application to the stereocontrolled synthesis of .beta.,.gamma.-unsaturated aldehydes and conjugated dienoic acids", published in Tetrahedron Lett. 1981, 22(1), 69-72, and abstracted in Chem. Abs. (1981), 95, 6442d. PA0 mono-unsaturated 2-hydroxyalkenoic acids, di-unsaturated 2-hydroxyalkenoic acids, and mono-unsaturated oxa-2-hydroxyalkenoic acids (i.e. ether acids). PA0 2-Hydroxy-4-nonenoic acid PA0 2-Hydroxy-4-decenoic acid PA0 2-Hydroxy-4-undecenoic acid PA0 2-Hydroxy-4-tridecenoic acid PA0 2-Hydroxy-4-tetradecenoic acid PA0 2-Hydroxy-4-pentadecenoic acid PA0 2-Hydroxy-4-hexadecenoic acid PA0 2-Hydroxy-4-heptadecenoic acid PA0 2-Hydroxy-4-octadecenoic acid PA0 2-Hydroxy-4-nonadecenoic acid PA0 2-Hydroxy-4-eicosenoic acid PA0 2-Hydroxy-4-heneicosenoic acid PA0 2-Hydroxy-4-docosenoic acid PA0 2-Hydroxy-4-tricosenoic acid PA0 2-Hydroxy-4-tetracosenoic acid PA0 2-Hydroxy-4-pentacosenoic acid PA0 2-Hydroxy-4-hexacosenoic acid PA0 2-Hydroxy-4-heptacosenoic acid PA0 2-Hydroxy-4-octacosenoic acid PA0 2-Hydroxy-4-nonacosenoic acid, and PA0 2-Hydroxy-4-triacontencoic acid. PA0 2-Hydroxy-4,7-octadienoic acid PA0 2-Hydroxy-4,9-decadienoic acid PA0 2-Hydroxy-4,10-undecadienoic acid PA0 2-Hydroxy-4,11-dodecadienoic acid PA0 2-Hydroxy-4,13-tetradecadienoic acid PA0 2-Hydroxy-4,15-hexadecadienoic acid PA0 2-Hydroxy-4,17-octadecadienoic acid PA0 2-Hydroxy-4,19-eicosadienoic acid PA0 2-Hydroxy-4,21-docosadienoic acid PA0 2-Hydroxy-4,23-tetracosadienoic acid PA0 2-Hydroxy-4,25-hexacosadienoic acid PA0 2-Hydroxy-4,27-octacosadienoic acid, and PA0 2-Hydroxy-4,29-triacontadienoic acid. PA0 2-Hydroxy-6-oxa-4-heptenoic acid PA0 2-Hydroxy-7-oxa-4-octenoic acid PA0 2-Hydroxy-9-oxa-4-decenoic acid PA0 2-Hydroxy-9-oxa-4-undecenoic acid PA0 2-Hydroxy-11-oxa-4-dodecenoic acid PA0 2-Hydroxy-13-oxa-4-tetradecenoic acid PA0 2-Hydroxy-13-oxa-4-pentadecenoic acid PA0 2-Hydroxy-14-oxa-4-pentadecenoic acid PA0 2-Hydroxy-13-oxa-14-methyl-4-pentadecenoic acid PA0 2-Hydroxy-11,14-dioxa-4-pentadecenoic acid PA0 2-Hydroxy-13-oxa-4-hexadecenoic acid PA0 2-Hydroxy-14-oxa-4-hexadecenoic acid PA0 2-Hydroxy-15-oxa-4-hexadecenoic acid PA0 2-Hydroxy-17-oxa-4-octadecenoic acid PA0 2-Hydroxy-14,17-dioxa-4-octadecenoic acid PA0 2-Hydroxy-18-oxa-4-eicosenoic acid PA0 2-Hydroxy-18-oxa-19-methyl-4-eicosenoic acid PA0 2-Hydroxy-19-oxa-4-docosenoic acid PA0 2-Hydroxy-18,21-dioxa-4-tricosenoic acid PA0 2-Hydroxy-22-oxa-4-tetracosenoic acid PA0 2-Hydroxy-25-oxa-4-hexacosenoic acid PA0 2-Hydroxy-24-oxa-4-heptacosenoic acid PA0 2-Hydroxy-25-oxa-4-octacosenoic acid PA0 2-Hydroxy-23,26-dioxa-4-octacosenoic acid, and PA0 2-Hydroxy-29-oxa-4-triacontenoic acid.
It is apparent that other 2-hydroxyalkenoic acids have not previously been disclosed in the literature, and an aspect of the invention is accordingly concerned with certain new 2-hydroxyalkenoic acids, and their synthesis.